Jeb Bush banned me from the bus. It was October 2014, two months before Jeb would announce he was exploring a run for president, and I had come to west Texas as an Associated Press reporter to ask about his plans. The former Florida governor had taken a day off from campaigning for midterm candidates to enjoy a victory lap with his son, George P. Bush, who was cruising to election as Texas land commissioner.

A Texas colleague and I were set to interview father and son aboard George P.’s campaign bus. But when the time came, one of George’s aides pulled me aside. As I watched my colleague enter the bus, the door closing behind him, I was told that neither I, nor my questions about the 2016 presidential race, would be allowed.

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Inside the bus, things weren’t much more freewheeling. As my colleague turned his questioning toward the upcoming campaign, Jeb stopped him. “You’re about ready to get a 15-yard penalty and loss of down here,” he said. “It's OK, but the flag's out.”

If that was a tiny snapshot of Jeb Bush’s need for tight control, his 2016 campaign has turned into an epic lesson. Not long after that bus incident in Texas, Jeb would boldly declare that he could upend the 2016 nomination process, avoid being drawn into the conservative gamesmanship of a primary and winnow the field with an unprecedented fundraising operation. His campaign called it “shock and awe,” and at the time it looked like a decisive statement of authority by a candidate whose time had come. But to people who’d seen the full arc of Bush’s career in politics, it also looked like something else: An admission that if Bush was going to win, he would need to control the race from the start.

Today, as his campaign struggles to break out of single digits in the polls, hoping for a rebound in New Hampshire, his supporters paint him as a tragic victim of the unforeseen Trumpocalypse. But Bush’s history suggests it’s equally conceivable that he would have struggled in a Donald-less campaign, where Ted Cruz, Chris Christie or Marco Rubio didn’t cooperate by simply backing down.

“He’s going toe to toe with people who are his peers, and he’s never had to do that, except for the one time he lost,” said Steve Schale, a Democratic strategist who oversaw his party’s legislative races during Bush’s governorship and helped run Barack Obama’s Florida campaigns. “He’s never had to deal with adversity in any real way. Governing was always like, ‘Hey, I want to do this.’”

What people missed, all along, is that Bush was never that strong a candidate; he was blessed with weak opponents in his two successful runs for governor and a Republican legislature eager to implement his agenda. And that has left him ill-prepared for the rigors of a modern presidential campaign, to say nothing of one with an activated anti-establishment electorate.

“He’s a very brittle campaigner who doesn’t handle the bully particularly well and feels most comfortable talking about policy with an electorate that has no appetite for policy,” said Dan Gelber, a Democratic leader in the Florida House during Bush’s administration. “It’s a combination of virtues and flaws that is giving him some serious ankle weights in this campaign.”

“He has been a very successful but reluctant politician,” said Mac Stipanovich, a Republican operative who advised Bush’s first campaign. “That is why he is a much better office holder, a much better public servant, than he is a campaigner.”

***

To those looking to understand Bush, the campaign to look at is 1994, the one year he ran for office against genuine competition. At the time, Bush was seen as the most promising son of America’s top Republican dynasty, though he eschewed his famous father’s moderate politics for Newt Gingrich’s firebrand conservatism. Facing a seven-way primary, he ran as a self-described “head-banging conservative,” which helped him clinch the nomination, but tripped him up in the general election.

It wasn’t the only thing that tripped him up. The rhetorical stumbles, wonkish demeanor and awkward humor that have defined Jeb’s flagging White House bid were on neon display in 1994. Women on welfare, Bush had said, “should be able to get their life together and find a husband.” Gays and lesbians, he said, do not deserve special legal protections because “we have enough special categories, enough victims, without creating even more.” Asked what he would do for African-Americans, he famously replied, “probably nothing.”

Back then, the provocateur needling him in the general election was Gov. Lawton Chiles, a 64-year-old Florida icon who literally walked from one end of the state to the other during his first U.S. Senate race. With crime rates up and taxes high, Chiles was vulnerable. Still, as he later did with Trump, Bush arguably underestimated his opponent.

In the race’s final stretch, the Democrat eviscerated Bush as inexperienced and hostile to minority and working-class voters. Half of Bush’s campaign haul came from events that either featured his parents or were sponsored by family friends, and Chiles said George and Barbara Bush were trying to buy Florida for their son.

“Jeb had never been punched in the nose before, and Lawton Chiles put him in a headlock and gave him the longest noogie ever,” Gelber said, “and with his hair messed up, his face red, he wasn’t sure what to do.”

Then, like now, Bush tried to take the high road, asking Chiles, “Don’t you feel a sense of shame for these things?” Chiles clearly did not. In fact, he seemed to delight in ripping Bush, albeit in a distinctively Southern way.

“I want to call attention to this old, liberal liar,” Chiles said, mocking one of Bush’s criticisms during their last debate. “The old he-coon walks just before the light of day.” Bush scanned the room and twiddled his thumbs, visibly baffled. But many in the crowd applauded, recognizing Chiles’s nod to Florida folklore, in which the oldest and wisest member of a raccoon pack knows when to strike.

That year’s November election brought a sweeping, national Republican victory, with the GOP taking control of the House, the Senate and state houses across the country. Amid the tidal wave of Gingrich’s GOP revolution, only two Republicans in America managed to lose high-profile statewide elections. One of them was Jeb Bush.

His takeaway: “Don’t run against someone who never lost,” he told the New York Times last month. “Find bad candidates.”

***

In Jeb lore, that 1994 defeat was a pivotal moment in the tale of an ambitious upstart who ran too hard to the right, alienated purple Florida and fell to a savvy rival. Failure, the story goes, enabled redemption. Out of personal and political crisis rose Jeb!, a champion of the downtrodden who, four years later, captured the governor’s office and ushered in Republican rule in Florida for the first time since Reconstruction. Jeb, they say, learned his lessons and became a better candidate.

All of this, while true, misses a crucial point: He never had to run a truly competitive race again. While Jeb did soften his tone in 1998 and campaigned aggressively in public schools and black churches (securing a remarkable 14 percent of the black vote), he did so amid incredibly favorable circumstances: Impressed by his near-win in 1994, the GOP establishment cleared the field for Bush. Without primary opposition, he amassed a multi-million-dollar war chest and courted voters with a more centrist message (arguably, a feat he tried—and failed—to replicate in 2016). Meanwhile, his Democratic opponent, Lt. Gov. Buddy MacKay, struggled to raise money, and the party succumbed to infighting. That allowed Bush to dominate the campaign.

“Jeb was the biggest personality in the race,” Stipanovich told me. “He was the press magnet. He was the sign of the political dynasty. He was the guy to cover. If you drew straws in the newsroom and you got Buddy MacKay, you lost.”

Bush whomped MacKay by 10 points.

In Tallahassee, the Republican legislature was eager to pass Jeb’s plans, or “big, hairy, audacious goals” —“BHAGs,” as he liked to call them. He pushed—and sometimes exceeded—the limits of executive power, and what little opposition he encountered, he steamrolled.

Campaigning for reelection in 2002, he found himself facing a potential voter backlash; he had eliminated affirmative action, overhauled public education and presided over a presidential election that ended in a polarizing recount, an outcome that helped send his brother to the White House. Democrats vowed revenge. But, in the absence of a strong statewide bench, they nominated a little-known Tampa lawyer named Bill McBride. Until the final month of the campaign, polls showed him within striking distance of Bush.

In the last debate, however, McBride stumbled badly—coming off, as Time magazine put it, as “a Bubba caught in the headlights” when he couldn’t explain how he would pay for a key campaign promise: smaller class sizes. Just as he did in last week’s debate when Rubio repeated talking points, Bush clearly benefited from an opponent’s mistake—then, he could show off his own mastery of policy—and from a huge war chest that allowed him to outspend McBride 4 to 1.

“Jeb really was on top of a huge juggernaut when he ran, and that fit him well,” says Gelber, the former Democratic leader. He would not be so lucky again.

***

Although Bush launched his presidential bid with an acknowledgment that “it’s nobody’s turn” and that he would have to “earn” the nomination, he has often chafed at the demands and tenor of that process. And while he insists he’s now more comfortable in the role of the underdog, he’s not a very scrappy one. (“Low energy,” Trump snarls.) His town halls can take on the air of therapy sessions: It’s clear he didn’t establish the parameters of the 2016 race, and he sure doesn’t like them.

“I’ve got a lot of really cool things I could do other than sit around being miserable, listening to people demonize me and me feeling compelled to demonize them,” he told a crowd in South Carolina in October. “That is a joke. Elect Trump if you want that.”

That was before he launched his “Jeb Can Fix It” tour, which, given his diminishing fortunes, seemed to be more a reference to his campaign than the country. Bush hired a well-known image-maker to help his debate performances, and recent dispatches from New Hampshire have indicated that he has improved as a campaigner: He seems more at ease, his delivery is crisper, he tells critics to get over “the Bush thing” and he says Trump is the “loser” who “needs therapy.” But overallhe can still come across as desperate, a man in search of an audience, an intellectual aghast at his rivals’ “lack of seriousness.”

Voters, headline writers and longtime friends have taken to using the same phrase for the former frontrunner, who finished sixth in the Iowa caucus and now faces a do-or-die vote in New Hampshire: “Poor Jeb.”

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“Please clap,” he implored a silent crowd in the Granite State last week, after delivering an impassioned national security pitch.

Throughout the campaign, he has been eclipsed by a crowd of hungrier and flashier competitors. It was only before Iowa, in the absence of Trump and all but ignored by the other candidates—and therefore permitted to talk about what he wanted, how he wanted —that he reemerged as a force on the debate stage.

Bush’s supporters, who are nothing short of apoplectic over Trump’s popularity, concede that today’s angry, hyperbolic debate is rough terrain for him, though they were heartened by his more aggressive posture in Saturday’s debate.

“So much of everything today is about presentation rather than substance,” Stipanovich said. Rubio, for instance, “pales standing next to Jeb in terms of experience. Yet he’s a better campaigner because he can make you believe that the fact that his dad was a bartender is a qualification for president of the United States. That’s not Jeb’s forte.”

But, perhaps more importantly, they acknowledge Jeb has done little to adapt to the circumstances, sticking to his “joyful,” policy-laden approach in a year defined by outrage. In fact, they count it as a virtue, a sign of authenticity in a field of phonies, a quality that could make the difference in New Hampshire and beyond.

“He’s not a performer. There are people in this race that are better performers,” said Cory Tilley, a former Bush aide in Tallahassee. “He is a doer, he is a problem solver, he is a hard worker. He has outlined policy solution after policy solution and plan after plan. That’s who he is. That’s what he does.”